Have you tried an open cup? Or an open cup with a straw? Both well-monitored of course. We had the best success with all of ours with open cups, especially Kid#3. Maybe by then we realized you don't really need a lid.

We tried so many different cups for our twins, but the best cup we found was the cheap-o $2 Nuby strawcups at WalMart. They have to work pretty hard to get it to leak. They takes falls from the table, etc very well. We've been using them nearly exclusively since my twins were 9-10ish months (27M now) and we've had two crack.

My twins also like the Camelbak kids cups, but I don't trust them. They'll leak just laying on their side and they can dump the whole cup of water out on themselves ina few seconds somehow!